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Communication | Regular issue | Vol 20, No. 11, 1983, pp.2163-2167
Published online, 1st January, 1970
DOI: 10.3987/R-1983-11-2163
Heterocyclic Substituted Amino Acids via α,β-Dehydroamino Acid Derivatives. Studies on Amino Acids III

Claus Herdeis and Ulrich Nagel

*Institut für Pharmazie und Lebensmittelchemie, Universität München, Sophienstraße 10, D-80333 München, Germany

Abstract

Condensations of lactam acetals 2a,b with isocyanacetic esters give 3a,b. The Z-configuration of 3a (R1=CH3, R2=C2H5) was determined by X-ray diffraction. Reaction with ethyl N-(ethoxycarbonyl)glycinate gives the protected α,β-dehydroamino acid derivatives 4. The isocyano group can be converted to the carbamate group via the isocyanates 5. Catalytic hydrogenation of the double bond and deprotection of the functional groups give the amino acids 11a, b and 10.